


The Oldest Profession

by CameronBlacksReads



Category: Supernatural
Genre: Anal Sex, Angst, Bottom Dean Winchester, Emotional Hurt/Comfort, Happy Ending, Hurt/Comfort, M/M, Modern AU, Prostitute Dean Winchester, Sex Worker, Sex Worker Dean Winchester, Smut, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester
Language: English
Status: In-Progress
Published: 2020-10-21
Updated: 2020-11-18
Packaged: 2021-03-09 06:20:06
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 5
Words: 8,065
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27129139
Author URL: https://archiveofourown.org/users/CameronBlacksReads/pseuds/CameronBlacksReads
Summary: Dean is happy with his life as a hooker. He loves feeling the night air on his face every night, and he is good at his job. One day he meets Castiel, the handsomest man he's ever seen with the ugliest car in the world, and everything changes.
Relationships: Castiel/Dean Winchester, Dean Winchester/Original Male Character(s), Dean Winchester/Other(s), Destiel
Comments: 14
Kudos: 58





	1. Chapter 1

**Author's Note:**

> Hey y'all! This is a new story I'm working on and I'm really excited about it. I'll try to post weekly. I have five chapters done, but its not finished. Hope you enjoy!

Dean felt alive tonight. It was a beautiful fall night in Kansas City, Kasas. The breeze was present enough that Dean didn’t feel like he was drowning in his own sweat, but it wasn't enough to make him cold. Dean was wearing his favorite pair of shorts, -- the jean ones that were obscenely short and tight -- this little black tight mesh top, and these little black heeled boots. He felt hot, and like he could take the whole world by storm.

Dean was leaning against the building talking to his girls.There were plenty of people working the street, but Dean, Hannah, Jo, and Charlie all stuck together. Dean and Charlie mostly worked regulars, -- Charlie the chicks and Dean the gay dudes-- while Hannah and Jo picked up most of the stragglers. That wasn’t to say that Dean didn’t leave with a stranger from time to time; he was the only male hooker this side of town.

Dean was chatting with Charlie, trying to look sexy leaning against a building and laughing hysterically at something she had said, and failing miserably, when the ugliest car Dean had ever seen pulled up. Jo sauntered up to the golden continental, exaggerating the swish of her hips, and leaned in the passenger window, wiggling her booty a little bit. Dean could tell the moment Jo got rejected because she dropped the sexy dance and adopted some more practical behaviors, like bending at the knees instead of the waist. She tapped the side of the car and walked back to the group.

“You’re up, Dean-o,” she announced. Dean pushed himself off of the wall he was leaning on and walked over to the car, throwing a wink over his shoulder at his friends.

When Dean walked up to the ugly-ass car, he took up Jo’s original position, resting his forearms on the open window. He looked in and was stunned.

The man sitting in the driver’s seat was absolutely breath-taking. He had this thick, dark hair that was sticking up every which way, and Dean couldn’t wait to get his fingers in it. Even sitting hunched over like the man was, Dean could tell the man was built like a ton of bricks. He had these big, elegant hands that were shakily rubbing up and down his thick thighs. His bright blue eyes kept flicking between Dean and the road in front of him, and he kept liking his plump, chapped lips.

Dean looked a little longer that he normally would have before he spoke. When he finally found the air to form words, he said, “Hey handsome. Looking for some company?” It was a cheesy line and he knew it, but Dean didn’t really care.

The man looked up at him hesitantly, meeting his eyes for a second before nodding. Dean opened the passenger side door and slid in. He buckled up and was busying himself with straightening his clothes, and he heard the man put the car in drive.

“So,” Dean began as the man started driving off, “where to?”

The man cleared his throat and said “My place,” and Dean just about died. Fuck, that man had a voice that was like wiskey and gravel and honey. If this guy got any sexier Dean’s soul might just leave his body and ascend to heaven without preamble.

“Okay,” Dean most definitely did not squeak out, “my name’s Dean, by the way.” 

“Castiel,” the man growls by way of response.

“Castiel, that's a cool name. Mind if I call you Cas?” Dean asks.

The man nodded and said nothing else. Dean suddenly feels awkward, and starts fidgeting with his hands. Dean never gets that way. If someone gives him a bad vibe then he can talk his way out of it, usually, and he can usually make conversation with everyone else, but this was different. Something about Cas was throwing Dean off his game; he felt like a teenager going on a date. And that was dumb because one, Dean was a professional, and two, he didn’t even know the guy or have any personal connection to him, so pre-date jitters shouldn’t be an issue. And yet, Dean’s mouth was as dry as the Sahara and his hands were sweating like crazy.

The two men sat in silence for the rest of the short drive. Cas pulled into a middle-class neighborhood, and pulled his ugly car into the garage of a much prettier house. Cas shut off the car and closed the garage door before he got out, and Dean took that as his cue to do the same.

Cas walked into the house, Dean on his heels, and they made their way to the kitchen. The house was a lot nicer on the inside than the outside. Every surface held expensive knick knacks and the walls were lined with framed artifacts. Some of the frames help pictures, and some held awards, while a couple had diplomas. There was not a speck of dust in sight, and Dean was very impressed. 

“Would you like something to drink?” Cas asked.

“Sure, man,” Dean responded, wringing his hands. He still felt weirdly on-edge with this man.

“So no offence, man,” Dean began, “but you're a good-looking guy, and I imagine you don’t have any problem scoring. So why do you need me?” Cas handed him a glass of water.

“Frankly, I don’t think that's any of your business.” Dean raised his hands in an “I surrender” gesture and drank his water. When they were done, Cas walked off and Dean followed. They walked to what Dean assumed was the master bedroom. Cas stood off to one side and waited expectantly.

“Okay, so I charge $150 an hour, anything fancy or not vanilla needs to be discussed beforehand, and we use Pretty Woman rules; no kissing on the lips. Sound good?” Cas nodded at Dean’s terms, and went to get his wallet. He pulled out $150 in cash and handed it to Dean. 

“I assume you want me to bottom?” Dean asked. Again, Cas nodded his head. Cas then started using his nimble fingers to unbutton his shirt.

Dean put the cash in the back pocket of his shorts for the time being, and pulled off his top. He was working on the button of his shorts when he caught a glimpse of Cas. His shirt was discarded and he was working on his belt, but his chest is what Dean focused on. The man had well-sculpted pacts and a firm middle. He didn’t look like one of those ‘roided up, dehydrated male models, but he looked like he was carved from marble. His shoulders were thick and well-defined, and they drew Dean’s attention to the man’s perfectly sculpted neck.

And now Dean was really confused. He was just starting to think that maybe Cas’ equipment was lacking, and that was why he needed to buy his pleasure, but then Cas pulled down his pants. He still had his boxer briefs on, but Dean could tell the man was hung.

Dean shook himself out of his trance and continued to undress. He pulled off his boots, then his shorts, and lastly the little g-string he wore. Dean walked over to his shorts and grabbed a condom and a little packet of lube that he always kept in his back pocket.

Dean was always prepared before the night began. He didn’t like to think of himself as a pessimist, but many of the guys he serviced were rough and inconsiderate, and he didn’t want to take chances.

So Dean laid down on the bed and pulled out his plug that had a big plastic jewel at the end of it. He set the plug next to him on the bed, and he lubed his fingers up just a bit. He was pretty stretched out, but he made sure he could comfortably fit four fingers inside himself, just in case. When he was done, he propped himself up on his elbows and saw Cas looking at him. The man’s eyes were dark, and he had a feral edge to his gaze. If Dean wasn’t turned on by Cas’ physique, that look would have had him rock hard. 

Dean didn’t like intimacy in these situations -- he just wanted to get a good fuck and move on with his life -- so he turned over onto his hands and knees, facing away from Cas. Cas also seemed like he wasn’t in the mood for pleasantries, because he grabbed Dean’s hips without preamble and lined his cock up with Dean’s entrance. Cas pushed in slowly but firmly, and stilled when he bottomed out. Even though Dean was used to this, he still always took a moment at this point to catch his breath. It was easier when he was turned on, but he still always tried to center himself.

Without warning, Cas started to slam in and out of Dean at a blinding pace. His hips slapped against Dean’s ass with every thrust, and for all of Dean’s efforts, he couldn’t breathe. Cas changed his angle slightly and he hit Dean’s prostate so hard that Dean cried out. Dean just sat there, panting and shaking after every one of Cas’ thrusts, only to be blown out of the water again and again.

Cas reached up and grabbed Dean by the neck and shoved his face into the bed. Dean’s breaths were stifled with the bedspread, and between that, the pressure on the back of his neck and the brutal pounding he was taking, Dean was just about in subspace. Dean almost never went there, partially through sheer will, but this was just too good.

As impossible as it seemed, Cas kept fucking harder and faster. Dean was limp at this point, just letting Cas do what he wants. He was so close; he could feel heat curling in his gut, and his toes following suit.

“Cas,” he choked out, barely audible over Cas’ grunting, “I’m close.”

In response, Cas picked up the pace yet again. With one adjustment of his hips, he nailed Dean’s prostate and Dean was flying over the edge. He moaned wantonly, spilling onto the comforter underneath him. As soon as the sensation passed, Dean collapsed under Cas’ weight. Cas just let him lay there, panting, and continued to chase his release. 

After several minutes of Dean feeling blissfully full and overstimulated, Cas’ hips lost their rhythm. He jerked, grinded, and then he stilled. Cas fell on top of Dean. The two men laid there, catching their breaths and coming down from their respective highs.

Eventually, Cas got off Dean. Dean heard him walk around, take the condom off, and throw it away. Dean laid there for just a moment longer, before he lifted himself off of the wet spot he had created.

“Bathroom?” he asked horsley. Cas pointed to an adjoining room. Dean went in there and washed himself off. His head still felt foggy, and he was trying to make all his faculties work again, but he couldn’t seem to pull himself together. It wasn’t that he was complaining; he felt fucking great, it was just different than what he was used to.

When Dean was done, he walked back to the bedroom to get dressed. He found Cas had removed the comforter, and was now laying underneath the sheets. Dean dressed quickly, and pulled some small bills out of his boot, where he kept them. Cas looked about as dead as Dean felt, and Dean didn’t see him moving any time soon.

When Dean was finally dressed and ready to go, he turned to Cas. “You’re a pretty good lay,” he said, “let's do this again sometime.” With that, Dean threw a wink over his shoulder and sauntered out of the room, scheduling an uber on his way out.


	2. Chapter 2

The next day Dean woke up late, as usual. But today he had way more energy than he normally did. Usually, he stumbled his way into the kitchen blindly and fumbled with the coffee machine until he had had at least two cups. But this morning he woke up and opened his eyes. If you knew Dean, that was unheard of. 

An hour, three cups of coffee and a huge breakfast later, it was only 10:00. Dean was freaking wired, and he had way too much time on his hands. So Dean started doing all the things he normally put off doing. 

One might not know it from looking at him, but Dean was very good with math. And Dean got paid in cash, so he sort of had to be. Anyway, he gathered all his cash from the last month and started sorting it. He had this system that he always used, and he always put it off because it was time consuming. Half of his monthly earnings went to Sam, and the other half he kept. Half of what he kept he put into savings and he didn’t touch that. The rest went to monthly expenses. His savings account was mostly for emergencies, like that one time Sam was strapped for cash because of school and Dean had to bail him out of a parking ticket. Sam was panicked, poor kid, ever the rule follower.

The money that went to Sam was incredibly important, so Dean paid extra at the post office to make sure it got to him safely. So once a month, Dean walked to the post office and paid some insane price to guarantee the package got there safely. Of course, this was counted as one of Dean’s monthly expenses.

He spent way too long there that morning, so by the time he walked out he was very annoyed, and the excess of caffeine did not help his mood. He was walking angrily towards the coffee shop next to the post office, using his frame that was best suited to a football player to get people to move out of his way, when he ran right into someone.

“Oh my god I’m so sorry I wasn’t -- Cas?” Dean met the fierce blue eyes of the man who had destroyed him last night, and he suddenly forgot his own name.

“I -- Dean?” Cas’s hand was on his chest still as he looked up at Dean, his brow furrowed and head tilted.

“What are you doing?” Dean asked super smartly.

“This, um, is my coffee shop. I come here every morning. My brother owns it.” Cas took his hand off Dean’s chest, and Dean finally took Cas in. He was wearing this black suit with a blue tie, and it hid all that perfectly sculpted flesh that Dean could picture exactly.

“Oh, um yeah. That makes sense.” “God Winchester,” Dean thought, “ pretend you’ve spoken to a human before.”

Both men stood there, not moving, and feeling decidedly awkward. Dean took a moment to steal himself, taking a deep breath.

“Listen Cas,” Dean began, “I’m sure this is not the kind of thing you want to hear and I totally understand if you say no, but I had a lot of fun last night. I’d love to do it again sometime, like as a real set up and not where one of us is being paid, so can I give you my number?” Dean’s eyes were scrunched shut and his shoulders were making out with his ears, and he couldn’t breathe, but he did it.

When Dean opened his eyes, Cas was looking at him with an unreadable expression on his face. Cas reached into the pants pocket of his suit, pulled out his phone, opened it, and handed it to Dean. The contacts app was open, so Dean took that as a yes.

Dean took the phone and started putting his info in there, when Cas said, “You give your number to all your john’s?”

Dean smirked, “Only the pretty ones.” He handed the phone back over.

“Thank you Dean. I’ll call you.” And with that, Castiel left.

***

It was weird for the first little while. Dean and Cas had such opposite work schedules, so it was hard to find convenient times to get together. Sometimes Dean would go over to Cas’s before he started working. Sometimes Dean went over before Cas went to work. At that point, it was mostly fucking when they both had a spare moment.

And there was another thing. They always went to Cas’s house. Dean preferred it that way, but after the first few times Cas started to not-so-subtly imply that he wanted to go to Dean’s place. Dean just played dumb and suggested they go to Cas’s place, and that was that. 

For their first real date, Cas asked Dean to breakfast at a local coffee shop on a Saturday morning. It wasn’t ideal for Dean -- Friday nights were busy and Dean had gotten very little sleep -- but it was Cas so he made it work and he was excited.

That morning, Dean got up way earlier than he should have. His stomach was in knots, so it wouldn’t let him sleep any longer. He spent a half hour in the shower, cleaning himself up and trying to force the warm water to relax him. Then he stood in front of all of his clothes for forty-five minutes, trying to decide what to wear. As much as Dean went on “dates” he couldn’t remember his last real date. And god, he liked Cas. He liked him with his whole being. He wanted to text him when he saw something funny, wake up to him in the morning, and rant to him when a john got too rough (he refrained from doing the last one, at least for the time being). And It seemed like Cas liked him too. Sometimes Dean said something funny and Cas would smile so hard that his gums showed and he would laugh so loud he would snort. Dean thought it was the cutest thing he’d ever seen.

Dean dressed in his tightest fitting jeans and a Led Zeppelin tee shirt. He put some gel in his hair and wished he was Jo so he could use the little makeup he owned to properly fix all his blemishes (that no one else could see, mind you. This was just an insecurity left over from his teenage years). By the time he deemed himself acceptable, he loaded up in his car, the most important thing in his life besides Sam, and made his way to the coffee shop.

When he walked in, he saw Cas sitting in a booth in the far left corner of the shop. Dean made his way over, and when Cas spotted him, he stood up for a greeting. The men embraced and Cas gave Dean a quick peck on the cheek.

“Heya Cas,” Dean said as he sat down.

“Hello Dean. You look wonderful.”

Dean blushed and said, “You don’t look too bad yourself, handsome.” And Cas didn’t. He had on a snug fitting, light grey, knit sweater that clung to him in all the right places, and some dark faded jeans. He looked like he had just walked out of a catalogue advertising perfect fall outfits, and Dean was desperate to get it off him.

The men chatted for a while, exchanging “how are you’s” and the like, before they ordered breakfast. Dean ordered the eggs benedict with the most meat on it, and Cas ordered a yogurt parfait.

“Friggin’ rabbit food. You and Sammy both,” Dean muttered as their server walked away.

“Excuse me?” Cas asked, raising his left eyebrow.

Dean swallowed. “Oh, it's just you and my brother both seem to have a thing for health food.”

“Is that so bad?” Cas asked, and the left side of his mouth twitched a little, so Dean knew he was sort of joking. “I just want to take care of myself.”

“Yeah, but at what cost, Cas? At what cost?” Cas chucked at Dean’s mock seriousness.

“So,” Cas began, “are you close with your brother?”

Dean smiled. “Yeah, me an’ Sam are thick as thieves. Our mom died when we were little and Dad wasn’t around much, so I practically raised the kid. He's great, really. He’s in law school at Stanford right now. He’s working his way through, and I’m sending him money every month, so he’s doing great.”

Cas looked pleased with this revelation. “So, is that why you, um, you know?”

“Yeah. Fast and easy cash. Best way to provide for him.” Cas pressed his lips together in what Dean took to be a pseudo smile. Time to change the subject, then. “I also pick up shifts at a local auto shop to make a little extra cash.”

“That’s nice,” Cas said, “so you like cars?”

“Yeah,” Dean smiled, “I mean you’ve seen my Baby. Cars have always been a thing for me.” Cas nodded.

“So Cas, what about you? Any family?” Cas’s expression became unreadable very quickly, and Dean thought he had made a mistake.

Before Dean could backtrack, Cas said, “I have a lot of family, actually. I just don’t talk to most of them. My older brother, Gabriel, is the only one I have any semblance of a relationship with. He’s the one who owns the shop where we bumped into each other.”

“So why didn’t we go there?” Dean asked, trying to lighten things a little. Cas rolled his eyes affectionately. 

“Because Gabriel would refuse to leave our side. Like, he would take a seat precariously close to being in your lap, and flirt with you until you felt like throwing up.”

Dean laughed, “Yeah, good call on that one.”

“He’s a good guy, and very well meaning,” Cas elaborated, “but it takes a certain type of person to be with him, and I have to be in a very specific mood to tolerate him. But he’s great, honest.”

“He sounds like a trip,” Dean said.

“He is.”

“Can I ask about the rest of your family?” Dean tried. He didn’t want to pry, but, hell, he was curious.

“They just --” Cas sighed, “they didn’t like the whole queer thing. Also, they were super religious and I may or may not have been incredibly outspoken against the church. They didn’t love that. We’ve sort of mutually agreed to only speak at weddings and funerals that we have to attend.”

“I’m sorry,” Dean said.

“That’s alright. It is what it is.” Cas looked down at the table and started fidgeting. 

“I have another question, If you don’t mind,” Dean said, raising his eyebrows. Cas spread his hands and looked expectant, so Dean continued. 

“You never did tell me why you came looking for a date that night.” Cas took on this sort of shy smile and ran a hand through his perpetually messy locks.

“I’m not great with the whole social thing,” Cas explained.

“Dean chuckled, “It seems like you're doing pretty great to me.”

“Thank you,” Cas smiled, “but this is easier. I didn’t have to make any real moves, ya know? Our first encounter was, well, it wasn’t difficult. After that, you made the move to exchange numbers. After those first interactions I usually feel more relaxed, but it's the getting there that is difficult.”

“I understand that,” Dean said. They sat and drank their coffee in silence for a while.

Then, Dean asked, “So, what do you do, Cas?” propping his chin on the heel of his hand.

“I’m a tax accountant for large businesses. Basically, I make sure they don’t ‘accidentally’ hoard large sums of money.”

“Did you seriously just use air quotes?” Dean chuckled, and his eyebrows almost touched his hairline. Cas furrowed his brow and almost looked offended.

“Anyway,” Dean course-corrected, “do you like what you do?”

Cas sighed, “I like it just fine. It is not the most fun thing, or what I pictured myself doing when I was younger, but it pays the bills, and it's fine. I've always been a bit of a math nerd, so I can get lost in the work.”

“That’s really cool,” Dean said, “I’ve never been an academic person. I dropped out in eleventh grade, and school just wasn’t my thing. Sam was always the smart one.”

“I’m sure that’s not true,” Cas responded sadly. “We all have our strengths, our intelligences. You maybe aren’t traditionally book-smart, but that doesn’t mean anything.”

“Yeah,” Dean said, wiggling his eyebrows, “my intelligence is sexual.” Dean stuck his tongue between his teeth and started rolling his body to some imagined beat. Just as Cas’s cheeks started to turn pink, and just before Dean started making obscene noises, their food came.

The men ate their meals quietly, chatting in between bites. They both commented on their orders, and exchanged pleasantries and jokes. When the check came, Dean made Cas arm wrestle for the bill, and Cas beat him handily. Dean gave up the bill (and may have found his loss incredibly hot), and they walked out of the coffee shop together. They shared a short goodbye kiss and went their separate ways.

**Notes for the Chapter:**

> Hope you enjoyed this! A comment or a kudos means you win my friendship forever. Come find me on Tumblr @I-know-like-four-things


	3. Chapter 3

**Notes for the Chapter:**

> Sorry this is short, but at least its fluffy for this fateful day in the United States. For my American readers, I hope you are taking care of yourselves and not too anxious.

Sundays were weird for Dean. A lot of the world was closed for the Day of Our Lord, Amen, but it was Dean’s busiest time of the week. Saturdays are, predictably, very busy. But so are Sundays, when men are tired of their wives dragging them to church, or gay men feel the hypocracy of the day, and want to act out on it. So Dean always took it easy before going out on Sundays, because he knew they could be wild.

He woke up a little past noon and decided that today was about coffee and Dr. Sexy, M.D. reruns. 

About half way through Dean’s third cup, he got a call from Sammy. 

“Heya Sammy. Whats up?” Dean answered.

“Not much. I just got the last package you sent, and so I wanted to give you a call and let you know. How are you?”

“Oh good. I’m just great, Sammy. Just great,” Dean’s smile was evident in his voice.

“Great? Wow, Dean. What's going on?”

“What, Sammy? Can’t your big brother just be happy from time to time?” Dean asked.

“No, not generally,” Sam laughed.

“Okay that’s valid,” Dean replied. “I kind of met someone.”

“You did?” Sam asked excitedly.

“Yeah. And it's not a big deal, it's not that serious or anything. But I really like him and I’m really happy.”

“Well,” Sam said, “I’m happy for you. Good for you, man.”

“Thanks Sammy.”

They talked for a while longer, exchanging stories. Sam told Dean about how school was going, and he gave updates on the girl he was seeing. Dean told Sammy about something funny he saw on tv, and didn’t talk about work. And they just went like that. They talked for at least an hour, maybe more, just catching up. It was like no time had passed since the last time they'd seen each other.

***

The girls noticed it too. That night, Dean was being extra saucy with everyone, especially the ones who weren’t interested in dates. Charlie loved it; she loved freaking people out, no matter what. Jo and Hannah, on the other hand, were more comfortable staying under the radar. Dean normally was, too, he tended to stick out like a sore thumb among all the ladies on the street as it was, but tonight he was more than willing to raise hell.

“Dean, what is going on with you? You’re like a whole different person,” Jo asked after Dean threw himself at a man who gave him a dirty look.

“What do you mean?” Dean asked, playing dumb.

“Dean. I have never seen you so happy, and I’ve known you forever,” Jo gave him a bitchface that rivaled Sammy’s.

“Yeah,” Charlie spoke up, “I agree. I haven’t seen you like this since the actor from Dr. Sexy released his phone number.”

“You know what guys? It's none of your business.” Dean crossed his arms over his chest, and leveled the three women with a glare that could kill.

Jo burst out laughing. “When has anything ever not been our business? You tell us about your bowel movements.”

Dean rolled his eyes and sighed. “You guys are going to think I’m so dumb.”

The woman sang a chorus of “Oh, Dean” and “No we won’t” and Dean almost felt confident about telling them.

“I’m kind of,” Dean took a deep breath, “seeing someone.” 

“Shut up,” Charlie yelled and punched him on the shoulder.

“Who is it?” Hannah asked, feigning disinterest.

“He’s, um, a guy I met on the job,” Dean winced. “Golden continental guy?”

“Oh. My. God.” Then Jo started hitting him. “You slept with a john? Is he paying you to be his boyfriend?”

“No, bitch! He paid me one time, on the first night, but now it's like a normal person relationship.” Dean started playing with his hands.

He felt a hand on his shoulder, he looked up to find it was Charlie, and the other girls were looking at him. “I’m happy for you, Winchester,” Charlie smiled. Jo and Hannah mumbled in agreement.

“Cool, cool, cool,” Dean patted Charlie and started walking away, “chick flick moment over. Let’s get back to work.”

**Notes for the Chapter:**

> Hope you enjoyed this! A comment or a kudos means you win my friendship forever. Come find me on Tumblr @I-know-like-four-things


	4. Chapter 4

**Notes for the Chapter:**

> I'm super sorry this episode is hella depressing. This is where the rape comes into play, so if that triggers you, just skip this chapter. I'll give a brief description of what happens at the end. If you do, you won't miss too much information, so you'll be able to read the rest with no problem. Stay safe everybody!

t was a Friday. Again, a very busy day, but Dean was feeling good. He had a breakfast date planned with Cas for the morning, so things were good. Dean was just walking back to his corner after a rendezvous in some dude’s car. He ran up behind Hannah and slapped her ass, and she punched him in the gut.

“Jesus, girl. Calm down, it's just me,” Dean wheezed.

Hannah rolled her eyes. “Why would that change anything?” She said.

“Ha. Ha.” Dean walked over to where Jo was standing. Apparently Charlie was occupied.

***

Dean spent a while throwing sultry looks at men who passed him by, and nothing was happening. This lull was so boring, and the part of his job that Dean hated.

Eventually, a guy started walking his way. He was a very big guy who looked like he had had a few too many. He had this sandy blonde hair, jeans that had more holes in them than a 16-year-old girl’s, and this jacket that Dean assumed was once green but was now a grey sort of color. He was walking towards Dean with this sauntering gait that Dean guessed was supposed to be sexy, but in reality it looked like one of his legs was numb and the other was stuck to a metal rod. Dean made eyes at the guy even though he really just wanted to laugh at him.

“Hey handsome,” Dean said when the man was within earshot, “you lookin for a date?”

“Yeah ,” the guy grumbled, avoiding eye contact like he was embarrassed.

“You got a place to go?” Dean asked, “A car, or a hotel room, or a house?” The guy shook his head. “M’kay.” Dean said.

Dean gestured for the guy to follow him while Dean walked to an alley that was usually empty. Usually Dean absolutely hated alley transactions; they made him feel dirty and awful. But a man’s gotta do what a man’s gotta do.

When they were finally alone, Dean turned his back to the wall and said “Alright. It’ll be $150 an hour. Everything else we have to talk about beforehand. No kissing on the lips. Sound good?”

The guy nodded and started digging through his pockets. He pulled out some cash and handed it to Dean, who put it in the back pocket of his shorts. 

“Alright,” Dean said, “let's do this thing.”

The guy crowded Dean against the wall and started groping him and kissing his neck. He reeked of alcohol and stale sweat. Dean started undoing the guy’s belt and pulling down his zipper. The guy started sucking on the bolt of Dean’s jaw and started getting awfully close to Dean's mouth. Dean started kissing the john’s neck in an effort to distract him, and the guy started kneading Dean’s ass.

The man started grinding on Dean and moaning while Dean kept sucking at his neck. The man put his hands on Dean’s shoulders, his palms hot and clammy. The man started pushing on Dean’s shoulders. Dean knew what he was looking for, but Dean just fought him on it.

The guy pushed until Dean’s legs couldn’t take it anymore, and Dean pulled himself off the guys neck. “Hey baby, want me to suck your dick? Wanna fuck my face?” The guy nodded, eyes looking dazed. “Okay, that is going to be $75 more.”

“Fuck that,” the guy said, shoving Dean harder.

“Hey,” Dean said sternly, “I said anything else would have to be discussed, okay? You agreed.”

Suddenly, the man’s eyes became clear, and Dean could see the muscles in his jaw clenching and unclenching. Dean tried to shrink back into the wall behind him, but there was no more room.

Without any warning, the guy punched Dean right in the face. Dean smacked his head against the wall with the force of it and felt like his head was filled with cement.

The man grabbed Dean by the shoulder and turned him around. Before Dean could even think about fighting back, the man shoved Dean’s face into the brick wall. Dean’s face started feeling warm and he tasted copper. He could feel the ridges of the brick rubbing against the spot on his cheek the man had hit.

God, Dean could barely open his eyes, but in the back of his mind he knew he should be panicking. He tried so hard to not let this happen. Dean usually had a good feel for creeps and he could avoid them, but it seemed like he fucked up big time.

The man grabbed Dean by the back of the neck and forced him into the wall. The man pulled him back and slammed his head back a couple more times for good measure. He grabbed the back of Dean’s pants and yanked them down. All Dean could do was think “run, man. Fight. Scream, panic, do something,” but his body wouldn’t respond. It was like the part of his brain that communicated his thoughts to his muscles had been severed. It was like having the world’s worst executive dysfunction. Dean felt like the human equivalent of a pile of wet towels.

The man got Dean’s shorts past his butt and was ripping the plug out and throwing it behind him. Dean could feel his pulse in every inch of his body and he also couldn’t breathe, but his head was way too cloudy to do anything about it.

Eventually Dean felt the blunt head of the man’s dick pushing against the entrance. Again, Dean thanked himself for prepping beforehand, but even so he felt dry and too stretched.

Dean was almost glad the man was holding him so tightly by the neck that Dean couldn’t see, because he wouldn’t have been able to stand up on his own. “I’m going to have to get an STD test in a few days. I guess I should also go back in a few months to double check,” Dean thought. Then he wondered if that was what shock felt like. He absently wondered why he wasn’t freaking out more.

The man was thrusting in and out roughly, and Dean absentmindedly felt sorry for whoever had to sleep with this guy because his technique was really unsatisfying. “I guess I have to sleep with him,” thought Dean. He wanted to chuckle, and then he decided that he was insane for wanting to do that. He felt the man’s thick cock thrusting in and out of him, his hips never moving. He had enough finesse as someone thrusting into a fleshlight. Dean could smell his awful stench, combined with the smell of urine.

After several minutes of that beautiful performance, the man’s rhythm started becoming uneven, and he finished in Dean’s ass. As soon as he rode out the aftershocks, the man pulled out and let go of Dean, who promptly fell down. Dean banged his elbow and his knee on the way down, and smacked his head again for good measure. “Fuck,” Dean thought, “this is going to be one hell of a concussion.”

Dean tried to open his eyes but they felt so heavy and he didn’t even remember closing them. He heard the man moving around behind him, and he was glad this was finally over.

With the sound of the zipper bringing a sort of finality to the situation, the man walked over and fumbled around in Dean’s shorts, and he took back his cash. He then promptly gave Dean a swift kick to the ribs. Now, Dean couldn’t see or breathe. Dean heard the sound of receding footsteps and felt the pressure in his chest and the throbbing in his face and neck. He started letting the rhythmic throbbing in his entire body overcome him, and eventually he fell into a fitful sleep.

**Notes for the Chapter:**

> For those of you who didn't read, Dean basically gets raped by a John. He is in shock the whole time. That's really all that happens; Cas is not in this chapter.


	5. Chapter 5

**Notes for the Chapter:**

> This chapter is hella angsty so be prepared. I swear this is gonna be a happy ending.
> 
> There are a couple points where Dean is reliving the rape, so be careful. I will put // before and \\\ after those sections for those of you who don't want to read those parts.

Dean woke up to a sunbeam shining right in his eyes. He squinted his eyes open and it took him a moment to remember last night's events. “Fuck,” was all he could think when he remembered.

He laid there for a moment, just pulling himself together enough to get up and face the world. God he was the fucking poster child for why you shouldn’t become a hooker. He proved every fucking guy right who told him that he was a worthless whore, who saw him on the street and gave him a dirty look, or worse, the people who looked at him with pity and asked what kind of sexual violence he has experienced that made him this way.

Dean didn’t get into this line of work because he was victimized, and now he felt like he was playing into every single stereotype in existence. How the hell was he supposed go back tonight, look Jo and Charlie and Hannah in the eye, and do his fucking job with dignity? How was he supposed to look at himself in the mirror every day? Fuck, how was he supposed to see Cas?

Dean sighed, and pushed himself up. He was super relieved to know that his pants were still down, and that he had been exposed all night, so that was good. He stood up and pulled his phone out of his pants pocket

6:17

“Okay,” Dean thought, “I have to meet Cas at 8:30 across town.”

Dean hustled to the parking lot where he kept Baby while he was working. If he was going to do this, he had to go home, clean himself up, and make himself look presentable before going on a date with Cas. God, Cas would be so disgusted if he found out what happened.

When Dean finally got to Baby, he broke every speeding law there was. He got back to his house in record time.

Dean’s first move was to go to the shower. Maybe that would help rid him of this disgusting gut feeling he had.

//

Dean got to the bathroom and stripped naked. The situation in his pants was … not good. Dean closed his eyes and took a deep breath. He started the shower. Dean took another breath and tried to calm himself down before taking a look in the mirror.

The whole side of his face was swollen and he could definitely see bruises forming. His cheekbone was a deep purple that progressed outward into an angry red, and blood was caked in the area where he assumed he had been hit. He could see the hints of bruises in the shape of fingertips curling around from the back of his neck.

That was certainly not a sight that encouraged hope, but Dean had to turn around a look at the damage done to his ass. Dean turned around, bent over slightly, and spread his cheeks. He grimaced at what he saw. There was definitely some tearing, as evidenced by the blood caked around his hole. The blood was mixed with dried cum, and the sight made Dean’s stomach turn. He turned back around, because he couldn’t stand to look at himself. 

Dean got in the shower and let the hot water pound into his shoulders, letting it wash the tension from his body. Dean let himself dissociate a little bit so he could go about cleaning himself up without losing his shit. Dean has handled this situation arguably well so far, if he did say so himself. He was not willing to let his composure go just yet.

\\\

When Dean had decided he was clean enough, he got out of the shower and toweled off. He wrapped the towel around his waist and walked into his bedroom trying to decide what to wear. He was torn between wanting to look good for his breakfast, and wanting to wear a potato sack to counteract the voice in his head that told him that, if he dressed less provocatively, last night wouldn’t have happened. Dean decided that that voice was dumb and he was going to look nice for the guy he was dating.

Dean took out his favorite boxer briefs, the kind that were well worn and cozy (and may or may not have had scooby doo characters on them), because he needed a bit of comfort today. He then selected a pair of dark wash jeans that weren’t too tight, but still made his ass look good. He also decided on a green long-sleeved henley that made his eyes look good. Dean took a deep breath and went to the bathroom to make his face look presentable.

His cheek was somehow darker, with more purple than red now. Dean had a little bit of emergency makeup for situations kind of like these, but he wasn’t sure if his limited supplies would cut it this time. He pulled out a yellowish eye-shadow thing and applied it all over his cheek, and then put concealer on over that. He stepped back to take a look at his handiwork.

It wasn’t … horrible. But it wasn’t great either. His eye still looked very swollen, as did his cheek, and the deep color of the bruise wasn’t completely hidden in the center. Dean’s lip was split, and he didn’t think there was anything to do about that. Dean thought that was as good as it was going to get, so he walked out of the bathroom with a sigh. 

By the time Dean was done getting ready, it was time to leave to meet Cas. He put in his favorite Led Zeppelin kassette in the stereo and turned it up loud to try to snap himself out of this sullen mood he was in. He pulled up to the restaurant at 8:27 and walked in, trying to convince himself that everything was fine.

He opened that door and immediately spotted Cas’ messy head of hair. He was at a table, facing away from the door, wearing a blue sweater and jeans. Dean walked up to him with shaking hands.

“Hey Cas,” Dean said, and then cleared his throat when his voice came out all raspy from not speaking all day.

Cas looked at him and got out of his seat, going to give Dean a hug. He pulled back for a kiss, but paused when he noticed the state of Dean’s face. 

“Dean, a-” Cas began, but Dean stopped him by patting his shoulder.

“It's okay Cas,” Dean said, “just got a little banged up.” Dean moved to the other side of the table to sit down.

Cas looked like he was in a daze. He moved to sit down, but his movements were rigid and unnatural. He didn’t seem present in the moment.

“What, um, what happened?” Cas asked, his brow twisting wildly.

“Oh, nothing. A john got a little rough last night, but I’m fine.”

“Really Dean?” Cas asked incredulously. 

“Yes Cas, I'm fine. It's just a part of the job.” Dean said, and picked up the menu, trying to signal that he wanted to change the subject.

Cas didn’t seem to get the picture. “Can we please talk about this, Dean?”

Dean sighed, “What is there to talk about?”

Cas fidgeted a little bit. “Look,” he began, “I have no issue with, you know, what you do. But if you are in danger, why don’t you just stop?”

“‘What I do’?” Dean repeated, “Cas, you can’t even say that I’m a hooker. You can’t even talk about it so you clearly aren’t okay with it. I don’t think you understand, but I’m not stopping.”

“Okay, maybe I don’t understand,” Cas said, “so explain it to me.”

“I like hooking, Cas. This is one of the few things I am good at, and it makes me feel good. Nights like last night are few and far between, but normally I feel free and powerful when I’m on the streets. I feel like I am making someone else feel good, so I must be doing something right. I am providing. Where is the problem with that?” Dean explained emphatically. His voice got louder as he continued speaking, and Cas was visibly tensing up with each word.

“Dean, you got hurt. You are putting yourself in harm's way. You are literally selling your body, Dean. That’s no life. You’re better than that.” Cas was almost yelling at that point.

Dean clenched and unclenched his jaw, and his whole body tensed, “Cas,” he said through gritted teeth, “stop. You don’t know what you’re talking about.”

“I have money, Dean,” Cas continued, ignoring Dean, “more than I know what to do with. I could help you get back on your feet. I can provide for Sam while you look for a real job.”

Dean practically had smoke blowing out of his ears. “A real job, Cas?” Cas closed his eyes and sighed.

“Dean, I didn’t mean --”

“You made it perfectly clear what you meant.”

“Dean,” Cas’s eyes were pleading, but he didn’t say anything else.

“You clearly can’t handle this. We’re done.” Dean slammed his hands on the table, standing up and storming out of the cafe. He got stares on his way out, but Dean couldn’t give a flying fuck at the moment.

He slid into the front seat of Baby and slammed on the steering wheel. “Sorry, Baby,” he said immediately, and started pulling his hair instead. Fuck, he was so angry at Cas. At most, he wanted someone to be angry for him, but this just felt like Cas was blaming him. He’d been fucking raped last night.

Rape. That was what happened. 

//

Dean sat back in his seat as the weight of what happened last night hit him. He couldn’t stop himself from remembering the way the rough skin of the man’s hands felt on the back of his neck. He could still smell the man’s hot breath on his cheek as he thrust into Dean. Fuck, Dean could remember the sound of the man’s skin slapping against his limp body.

Dean felt hot tears slide down his cheeks, and his stomach clenched painfully. He stayed in the car for what felt hours, playing last night over and over again, and repeating to himself I was raped, I was raped.

\\\

He was ripped out of his reverie by a knocking on his window. He looked up and saw Cas standing there, looking pitiful. Dean angrily wiped his face, horrified that Cas saw him crying, and was probably thinking it was about him. Dean jammed the key in the ignition and started the car, and then pulled out of the parking spot, making Cas jump out of the way.

Dean wasn’t an animal person, but this was one of the moments that made him wish he had a pet. He got home and had this empty feeling in his stomach, and he wished he could just curl up with a furry friend who wouldn’t judge him no matter what he did.

Instead, he sent a vague text to Sammy and curled up on the couch with his favorite blanket, and turned on Dr. Sexy. That was how he spent the rest of his day; trying to distract himself from his thoughts until he passed out on the couch.

**Author's Note:**

> Hope you enjoyed this! A comment or a kudos means you win my friendship forever. Come find me on Tumblr @I-know-like-four-things


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